Selective C-H dithiocarbamation of arenes and antifungal activity evaluation

Org Biomol Chem. 2020 Feb 19;18(7):1369-1376. doi: 10.1039/c9ob02514f.

Abstract

This paper discloses a transition metal-free selective C-H dithiocarbamation of drug skeletons using disulfiram (DSF) in the presence of KI/K2S2O8 in DMF/H2O. Drug skeletons, including 5-aminopyrazoles, indoles, pyrroloquinoline, and Julolidine, underwent C-H dithiocarbamation smoothly to afford a variety of drug-like molecules in moderate to good yields. It was found that the in situ formed 5-aminopyrazole iodide is the key intermediate for the dithiocarbamation. Bioassay results show that some of these N-heterocyclic dithiocarbamate derivatives exhibit good antifungal activity against Colletotrichum gloeosprioides and Fusarium oxysporum, F. proliferatum, Fusarium solani, Geotrichum candidum, Penicillium digitatum, Penicillium italicum, Phyricularia grisea.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Antifungal Agents / chemical synthesis
  • Antifungal Agents / chemistry
  • Antifungal Agents / pharmacology*
  • Benzene Derivatives / chemistry
  • Colletotrichum / drug effects*
  • Fusarium / drug effects*
  • Geotrichum / drug effects*
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Penicillium / drug effects*
  • Stereoisomerism
  • Thiocarbamates / chemical synthesis
  • Thiocarbamates / chemistry
  • Thiocarbamates / pharmacology*

Substances

  • Antifungal Agents
  • Benzene Derivatives
  • Thiocarbamates